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CN101490759A - Ultraviolet-curable resin composition and use thereof - Google Patents

Ultraviolet-curable resin composition and use thereof Download PDF

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Publication number
CN101490759A
CN101490759A CNA2007800261936A CN200780026193A CN101490759A CN 101490759 A CN101490759 A CN 101490759A CN A2007800261936 A CNA2007800261936 A CN A2007800261936A CN 200780026193 A CN200780026193 A CN 200780026193A CN 101490759 A CN101490759 A CN 101490759A
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CN
China
Prior art keywords
resin combination
acrylate
methyl
optical disk
ultraviolet ray
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Granted
Application number
CNA2007800261936A
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Chinese (zh)
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CN101490759B (en
Inventor
小林大祐
德田清久
内藤正弘
水谷刚
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Nippon Kayaku Co Ltd
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Nippon Kayaku Co Ltd
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Publication of CN101490759A publication Critical patent/CN101490759A/en
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Publication of CN101490759B publication Critical patent/CN101490759B/en
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    • G—PHYSICS
    • G11—INFORMATION STORAGE
    • G11B—INFORMATION STORAGE BASED ON RELATIVE MOVEMENT BETWEEN RECORD CARRIER AND TRANSDUCER
    • G11B7/00—Recording or reproducing by optical means, e.g. recording using a thermal beam of optical radiation by modifying optical properties or the physical structure, reproducing using an optical beam at lower power by sensing optical properties; Record carriers therefor
    • G11B7/24—Record carriers characterised by shape, structure or physical properties, or by the selection of the material
    • G11B7/241—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material
    • G11B7/252—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of layers other than recording layers
    • G11B7/257—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of layers other than recording layers of layers having properties involved in recording or reproduction, e.g. optical interference layers or sensitising layers or dielectric layers, which are protecting the recording layers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F222/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
    • C08F222/10—Esters
    • C08F222/1006—Esters of polyhydric alcohols or polyhydric phenols
    • C08F222/102—Esters of polyhydric alcohols or polyhydric phenols of dialcohols, e.g. ethylene glycol di(meth)acrylate or 1,4-butanediol dimethacrylate
    • G—PHYSICS
    • G11—INFORMATION STORAGE
    • G11B—INFORMATION STORAGE BASED ON RELATIVE MOVEMENT BETWEEN RECORD CARRIER AND TRANSDUCER
    • G11B7/00—Recording or reproducing by optical means, e.g. recording using a thermal beam of optical radiation by modifying optical properties or the physical structure, reproducing using an optical beam at lower power by sensing optical properties; Record carriers therefor
    • G11B7/24—Record carriers characterised by shape, structure or physical properties, or by the selection of the material
    • G11B7/241—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material
    • G11B7/252—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of layers other than recording layers
    • G11B7/256—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of layers other than recording layers of layers improving adhesion between layers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10—Esters
    • C08F220/12—Esters of monohydric alcohols or phenols
    • C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
    • C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
    • C08F220/1812—C12-(meth)acrylate, e.g. lauryl (meth)acrylate
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10—Esters
    • C08F220/26—Esters containing oxygen in addition to the carboxy oxygen
    • C08F220/28—Esters containing oxygen in addition to the carboxy oxygen containing no aromatic rings in the alcohol moiety
    • C08F220/281—Esters containing oxygen in addition to the carboxy oxygen containing no aromatic rings in the alcohol moiety and containing only one oxygen, e.g. furfuryl (meth)acrylate or 2-methoxyethyl (meth)acrylate
    • G—PHYSICS
    • G11—INFORMATION STORAGE
    • G11B—INFORMATION STORAGE BASED ON RELATIVE MOVEMENT BETWEEN RECORD CARRIER AND TRANSDUCER
    • G11B7/00—Recording or reproducing by optical means, e.g. recording using a thermal beam of optical radiation by modifying optical properties or the physical structure, reproducing using an optical beam at lower power by sensing optical properties; Record carriers therefor
    • G11B7/24—Record carriers characterised by shape, structure or physical properties, or by the selection of the material
    • G11B7/2403—Layers; Shape, structure or physical properties thereof
    • G11B7/24035—Recording layers
    • G11B7/24038—Multiple laminated recording layers
    • G—PHYSICS
    • G11—INFORMATION STORAGE
    • G11B—INFORMATION STORAGE BASED ON RELATIVE MOVEMENT BETWEEN RECORD CARRIER AND TRANSDUCER
    • G11B7/00—Recording or reproducing by optical means, e.g. recording using a thermal beam of optical radiation by modifying optical properties or the physical structure, reproducing using an optical beam at lower power by sensing optical properties; Record carriers therefor
    • G11B7/24—Record carriers characterised by shape, structure or physical properties, or by the selection of the material
    • G11B7/241—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material
    • G11B7/242—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers
    • G11B7/244—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers comprising organic materials only
    • G11B7/246—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers comprising organic materials only containing dyes
    • G11B7/2467—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers comprising organic materials only containing dyes azo-dyes
    • G—PHYSICS
    • G11—INFORMATION STORAGE
    • G11B—INFORMATION STORAGE BASED ON RELATIVE MOVEMENT BETWEEN RECORD CARRIER AND TRANSDUCER
    • G11B7/00—Recording or reproducing by optical means, e.g. recording using a thermal beam of optical radiation by modifying optical properties or the physical structure, reproducing using an optical beam at lower power by sensing optical properties; Record carriers therefor
    • G11B7/24—Record carriers characterised by shape, structure or physical properties, or by the selection of the material
    • G11B7/26—Apparatus or processes specially adapted for the manufacture of record carriers
    • G11B7/263—Preparing and using a stamper, e.g. pressing or injection molding substrates

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Optical Record Carriers And Manufacture Thereof (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Manufacturing Optical Record Carriers (AREA)
  • Macromonomer-Based Addition Polymer (AREA)

Abstract

Disclosed is an ultraviolet-curable resin composition for multilayer optical discs, which contains (A) dioxane glycol di(meth)acrylate and/or tricyclodecane dimethylol di(meth)acrylate, and (B) a photopolymerization initiator.

Description

Ultraviolet ray-curable resin combination and uses thereof
Technical field
[0001] the present invention relates to ultraviolet ray-curable resin combination, so that in multiplayer optical disk, form transparent resin intermediate layer and have the multiplayer optical disk of the cured product of said composition as transparent resin intermediate layer with two-layer at least recording layer.
Background technology
[0002] these years in, to the demand phenomenal growth of jumbo CD.The technical examples that increases the video disc recording capacity comprises the method that adopts shorter wavelength recoding/reproduction light beam, in recoding/reproduction beam irradiation optics system, be used for object lens higher NA (number of pores) method and be used for the multilevel method of recording layer.In the middle of these, and adopt shorter wavelength or adopt the situation of higher NA to compare, the multilayer that is used for recording layer makes CD have big capacity under lower cost.
For example, have the DVD of two-layer recording layer or HD-DVD dish and adopt the structure of wherein two-layer recording layer with between two parties transparent resin intermediate layer lamination.Particularly, make lamination in the following sequence from the observed structure of the light incident side of recoding/reproduction light beam: the transparent resin substrate of a 0.6mm, first recording layer, the first translucent reflection horizon, transparent resin intermediate layer, second recording layer, second reflection horizon, the transparent resin substrate of adhesive phase and the 2nd 0.6mm; Formation transparent resin intermediate layer wherein as described below: apply on the translucent reflection horizon of resin combination to the first of ultraviolet ray-curable, facing to transparent resin punch die extruding with uneven pattern and employing ultraviolet photo-curing, wherein said uneven pattern comprises the guide channel of guiding recoding/reproduction light beam, discharge punch die afterwards, and and then with rough design transfer to the surface of cured product, form transparent resin intermediate layer.
[0003] from observed structure feasible photic zone, first recording layer, first translucent reflective layer, transparent resin intermediate layer, second recording layer, second reflection horizon and the 1.1mm resin base of lamination: 0.1mm in the following sequence of the light incident side of recoding/reproduction light beam with blu-ray CD of two-layer recording layer; Formation transparent resin intermediate layer wherein as described below: the resin combination that applies ultraviolet ray-curable is to second recording layer, facing to transparent resin punch die extruding with uneven pattern and employing ultraviolet photo-curing, wherein said uneven pattern comprises the guide channel of guiding recoding/reproduction light beam, discharge punch die afterwards, and and then with rough design transfer to the surface of cured product, form transparent resin intermediate layer.
[0004] usually, above-described transfer method is called as 2P (photopolymerization) method and employed ultraviolet ray in the 2P method-curable resin combination is called as the 2P resin.
The example that is used for the resin of transparent resin punch die comprises acryl resin, methacrylic resin, polycarbonate resin, polyolefin resin (especially, amorphous polyolefin), vibrin, polystyrene resin and epoxy resin.The performance of 2P resin after solidifying, for example demolding performace, low moisture pick-up properties and the angle of shape stability are considered, especially preferably amorphous polyolefin; Consider from the angle of material cost, especially the optimization polycarbonate resin.
Usually, polycarbonate resin is used for the resin base of 0.6mm and is used for the resin base of 1.1mm in the blu-ray CD in DVD or HD-DVD CD.When polycarbonate resin is used as the transparent resin punch die, applies the ultraviolet ray-curable resin that is different from the 2P resin and will promote the resin punch die of making by polycarbonate from the 2P resin bed that has cured, to discharge to the resin-based bottom side.
[0005] the desired performance of 2P resin is as described below:
(i) performance of the Man Yi demoulding from the transparent resin punch die;
The (ii) Man Yi performance that from the transparent resin punch die, shifts;
(iii) the warpage of optical disc substrate is little after ultraviolet curing;
(iv) not distortion of the uneven pattern that under high temperature and high humility, shifts; With
(v) especially in CD, under high temperature and high humility, there is not dye diffusion to arrive in the transparent resin intermediate layer with recording layer of making by dyestuff.
The poor performance of the demoulding makes transparent resin intermediate layer peel off with the transparent resin punch die from the transparent resin punch die, causes defective.The transfer performance of difference causes mistake occurs when recoding/reproduction.The big warpage of optical disc substrate causes following problems after ultraviolet curing: can not be formed uniformly recording layer or reflection horizon on formed rough pattern; The lamination of second substrate is interfered under DVD or HD-DVD CD situation; With under blu-ray CD situation, the euphotic even formation of 0.1mm is interfered.And the distortion of uneven pattern or dye diffusion cause record performance inhomogeneous (for example, shake (jitter) performance) between first and second recording layers in transparent resin intermediate layer under high temperature and high humility.
When using metal die, has the formation of uneven pattern on the substrate of glass of metal die in the 2P resin experience described in any one piece of the patent documentation 1-4; None discloses these patent documentations employing transparent resin punch die and has formed uneven pattern.In addition, patent documentation 5-8 comprises the description of 2P resin separately but does not comprise any explanation of resin of the present invention.
[0006]
Patent documentation 1:JP-A-5-59139
Patent documentation 2:JP-A-5-132534
Patent documentation 3:JP-A-5-140254
Patent documentation 4:JP-A-5-132506
Patent documentation 5:JP-A-2003-331463
Patent documentation 6:JP-A-2004-288242
Patent documentation 7:JP-A-2004-288264
Patent documentation 8:JP-A-2005-332564
Disclosure of the Invention
[0007] the purpose of this invention is to provide ultraviolet ray-curable resin combination, it obtains cured product in multiplayer optical disk, described cured product is good aspect the transfer performance of the uneven pattern of transparent resin punch die and in the function admirable of the demoulding from the transparent resin punch die with therefore obtain permanance and dye diffusion and suppress all high multiplayer optical disk of ability.
Therefore [0008] inventor has constantly carried out deep research, so that solve above-described problem and by finding that the ultraviolet ray-curable resin combination with specific composition is suitable for the 2P resin, thereby realizes the present invention.
[0009] more specifically, the present invention relates to following aspect (1)-(11).
(1) be used for the ultraviolet ray-curable resin combination of multiplayer optical disk, it comprises:
(A) diox glycol two (methyl) acrylate and/or tristane dihydroxymethyl two (methyl) acrylate and
(B) Photoepolymerizationinitiater initiater.
(2) according to the ultraviolet ray that the is used for multiplayer optical disk-curable resin combination of (1), it comprises that further (C) has the compound of at least two (methyl) acryloyl groups in its molecule.
(3) according to the ultraviolet ray that the is used for multiplayer optical disk-curable resin combination of (2), it comprises the weight with respect to whole resin combination, 15-85wt% (A) component, 0.1-10wt% (B) component, and 10-80wt% (C) component.
(4) according to the ultraviolet ray that the is used for multiplayer optical disk-curable resin combination of (2), it further comprises (D) single (methyl) acrylate compounds.
(5) ultraviolet ray that the is used for multiplayer optical disk-curable resin combination of basis (4), it comprises the weight with respect to whole resin combination, 15-85wt% (A) component, 0.1-10wt% (B) component, 8-80wt% (C) component, and 5-40wt% (D) component.
[0010]
(6) according to any one the ultraviolet ray that is used for multiplayer optical disk-curable resin combination of (2)-(5), the compound (C) that wherein has two or more at least (methyl) acryloyl group in its molecule comprises one or more in the poly-propoxyl group diacrylate of trimethylolpropane triacrylate, pentaerythritol triacrylate, double trimethylolpropane tetraacrylate, three [acryloxy ethyl] isocyanuric acid ester, dipentaerythritol acrylate, tripropylene glycol diacrylate and neopentyl glycol.
(7) according to any one the ultraviolet ray that is used for multiplayer optical disk-curable resin combination of (4)-(6),, wherein (D) single (methyl) acrylate compounds comprises one or more in dicyclopentenyl dipheny oxide base ethyl propylene acid esters, lauryl acrylate and the methoxyl tripropylene glycol acrylate.
(8) according to any one the ultraviolet ray that is used for multiplayer optical disk-curable resin combination of (1)-(4), wherein Photoepolymerizationinitiater initiater (B) is 1-hydroxycyclohexylphenylketone or 2,4,6-trimethylbenzoyl diphenyl phosphine oxide.
(9) according to any one the ultraviolet ray that is used for multiplayer optical disk-curable resin combination of (1)-(5), wherein adopting Brookfield viscometer is 30-800mPas in the viscosity of 25 ℃ of compositions of measuring down.
(10) by with photochemical x ray irradiation x according to any one the cured product that the ultraviolet ray that is used for multiplayer optical disk-curable resin combination obtains of (1)-(6).
(11) a kind of multiplayer optical disk, it comprises the cured product according to (10).
[0011] ultraviolet ray of the present invention-curable resin combination can provide transparent resin intermediate layer in the multiplayer optical disk with two-layer at least recording layer, described transparent resin intermediate layer is aspect the transfer performance of the uneven pattern of transparent resin punch die and all good at the aspect of performance of the demoulding from the transparent resin punch die.And, have the multiplayer optical disk of this transparent resin intermediate layer even under high temperature and high humility, demonstrate permanance and multiplayer optical disk that dye diffusion suppresses ability and therefore can stably obtain to have satisfied throughput rate.
Implement optimal mode of the present invention
[0012] hereinafter will describe the present invention in detail.Employed in the present invention (A) component, that is diox glycol two (methyl) acrylate and/or tristane dihydroxymethyl two (methyl) acrylate are for guaranteeing the desired performance of above-described 2P resin (i)-(v) be important.， diox glycol two (methyl) acrylate is from the function admirable by the demoulding the transparent resin punch die of polycarbonate resin one-tenth especially.
As diox glycol two (methyl) acrylate, can use commercially available product, the example of this commercially available product comprises KAYARAD R-604 (by Nippon Kayaku Co., Ltd. makes).
As tristane dihydroxymethyl two (methyl) acrylate, can use commercially available product, the example of this commercially available product comprises KAYARAD R-684 (by Ni ppon KayakuCo., Ltd. makes).
When diox glycol two (methyl) acrylate and tristane dihydroxymethyl two (methyl) acrylate used with form of mixtures, its mixing ratio can randomly change according to the rough pattern of the shape (warpage) of first substrate and resin punch die.Preferably, this potpourri is made up of 3-97wt% tristane dihydroxymethyl two (methyl) acrylate and 97-3wt% diox glycol two (methyl) acrylate.
With respect to the weight of the whole resin combination of the present invention, employed (A) component is generally 10-98wt% and preferred 15-85wt%.When consumption during less than 10wt%, but the performance deterioration that from the transparent resin punch die, shifts, and perhaps the warpage of optical disc substrate may be bigger; When consumption during greater than 98wt%, curability may be not enough.
[0013] example of employed Photoepolymerizationinitiater initiater (B) component comprises in the present composition: benzophenone; the 1-hydroxycyclohexylphenylketone; 2-hydroxy-2-methyl-1-phenyl-third-1-ketone; 2; 2-dimethoxy-1; 2-diphenyl second-1-ketone; 2-methyl isophthalic acid-[4-(methyl mercapto) phenyl 1-2-morpholino third-1-ketone; 2-benzyl-2-dimethylamino-1-(4-morpholinyl phenyl)-Ding-1-ketone; two (2; 6-dimethoxy benzoyl)-2; 4; 4-tri-methyl-amyl phosphine oxide; two (2; 4; the 6-trimethylbenzoyl) phenyl phosphine oxide and 2; 4,6-trimethylbenzoyl phosphine oxide.Preferred 1-hydroxycyclohexylphenylketone and 2,4,6-trimethylbenzoyl phosphine oxide, the performance of the two demoulding in the transparent resin punch die all is satisfied.
With respect to the weight of the whole resin combination of the present invention, the consumption of employed Photoepolymerizationinitiater initiater (B) component is generally 0.1-10wt% and preferred 1-8wt%.When consumption less than 0.1% the time, curability may be not enough and when consumption during greater than 10wt%, the possible deterioration of the performance of the demoulding from the transparent resin punch die.
In addition, can use Photoepolymerizationinitiater initiater in conjunction with curing accelerator.The instantiation of the curing accelerator that can be used in combination comprises amine, for example triethanolamine and diethanolamine; And hydrogen donor, for example mercaptobenzothiazoler.With respect to the weight of the whole resin combination of the present invention, the consumption of the curing accelerator that is used in combination is generally 0.2-5wt%.
[0014] employed among the present invention (C) component, that is the compound that has at least two (methyl) acryloyl groups in its molecule is used to improve suppresses the purpose of dye diffusion in the transparent resin intermediate layer under high temperature and high humility.(C) example of component comprises: tripropylene glycol diacrylate; 1; 6-hexanediol two (methyl) acrylate; neopentyl glycol two (methyl) acrylate; 1; 9-nonanediol two (methyl) acrylate; neopentyl glycol gathers propoxyl group two (methyl) acrylate; hydroxy new pentane acid neopentyl glycol two (methyl) acrylate; polymer with bis phenol A ethoxy two (methyl) acrylate; Bisphenol F polyethoxy two (methyl) acrylate; polyglycol two (methyl) acrylate; two [(methyl) acryloxy ethyl] hydroxyethyl isocyanuric acid ester; trimethylolpropane tris (methyl) acrylate; trihydroxy methyl octane three (methyl) acrylate; trimethylolpropane polyethoxy three (methyl) acrylate; trimethylolpropane gathers propoxyl group three (methyl) acrylate; the trimethylolpropane polyethoxy gathers propoxyl group three (methyl) acrylate; three [(methyl) acryloxy ethyl] isocyanuric acid ester; pentaerythrite three (methyl) acrylate; pentaerythrite polyethoxy four (methyl) acrylate; pentaerythrite gathers propoxyl group four (methyl) acrylate; pentaerythrite four (methyl) acrylate; double trimethylolpropane four (methyl) acrylate; dipentaerythritol four (methyl) acrylate; dipentaerythritol five (methyl) acrylate; dipentaerythritol six (methyl) acrylate; dipentaerythritol five (methyl) acrylate of caprolactone modification; dipentaerythritol six (methyl) acrylate of caprolactone modification; three [(methyl) acryloxy ethyl] isocyanuric acid ester of caprolactone modification, and have the compound of hydroxyl and two or more (methyl) acryloyl groups and have reaction product between the compound of two or more isocyanate group.Especially preferred trimethylolpropane triacrylate (KAYARAD TMPTA, by NipponKayaku Co., Ltd. make), pentaerythritol triacrylate (KAYARAD PET-30, by Nippon Kayaku Co., Ltd. make), double trimethylolpropane tetraacrylate (KAYARADT-1420 (T), by Ni ppon Kayaku Co., Ltd. makes), three [acryloxy ethyl] isocyanuric acid ester (M-315, by Toa Gosei Co., Ltd. makes), dipentaerythritol acrylate (KAYARAD DPHA, by Nippon Kayaku Co., Ltd. make), tripropylene glycol diacrylate and neopentyl glycol gather propoxyl group diacrylate (New Frontier NPG-2P, by Dai-ichiKogyo Seiyaku Co., Ltd. makes).
With respect to the weight of the whole resin combination of the present invention, employed (C) component is generally 8-80wt%, preferably 10-80wt% and more preferably 12-75wt%.When consumption is less than or equal to 8wt%, under high temperature and high humility, suppress the effect deterioration of dye diffusion and when consumption during greater than 80wt%, cross-linking density can increase and the warpage of CD may be bigger.
[0015] (D) used in the present invention component, that is three (methyl) acrylate compounds has the performance that reduces disc tilt.(D) example of component comprises tristane (methyl) acrylate, dicyclopentenyl oxygen base ethyl (methyl) acrylate, two cyclopentyl (methyl) acrylate, isobornyl (methyl) acrylate, adamantyl (methyl) acrylate, lauryl acrylate, methoxyl tripropylene glycol (methyl) acrylate, phenoxy group ethyl (methyl) acrylate, benzyl (methyl) acrylate, (methyl) tetrahydrofurfuryl acrylate, the morpholine acrylate, phenyl glycidyl base (methyl) acrylate, 2-hydroxyl (methyl) acrylate and 2-hydroxyl-3-phenoxy propyl (methyl) acrylate.Especially preferred dicyclopentenyl oxygen base ethyl propylene acid esters, lauryl acrylate and methoxyl tripropylene glycol acrylate.These compounds can use with optional ratio separately or with two or more potpourris separately.
With respect to the weight of whole resin combination of the present invention, the consumption of employed (D) component is generally 5-40wt% and preferred 10-30wt%.When consumption during more than or equal to 5wt%, the warpage of CD descends and when consumption during greater than 40wt%, the possible deterioration of curability.
[0016] in the present invention, (A) and (B) component be under the situation of resin combination of solvent, (A) and (B) ratio of component can be respectively the weight with respect to whole resin combination, about 10-98wt% and about 0.1-10wt%.
On the other hand, (A), (B) and (C) component be under the situation of resin combination of solvent, (A), (B) and (C) ratio of component can be respectively weight with respect to whole resin combination, about 15-85wt%, about 0.1-10wt% and about 10-80wt%.
On the other hand, (A), (B), (C) and (D) component be under the situation of resin combination of solvent, (A), (B), (C) and (D) ratio of component can be respectively weight with respect to whole resin combination, about 15-85wt%, about 0.1-10wt%, about 8-80wt% and about 5-40wt%.
[0017] in addition, in the present invention, optionally can use epoxy acrylate, urethane acrylate, polyester acrylate and polycarbonate acrylic ester compounds.
[0018] in addition, in the present invention, except above-described component, can optionally be used in combination following additives: silane coupling agent, levelling agent, defoamer, polymerization inhibitor, light stabilizer (for example, hindered amine), antioxidant, antistatic agent, surface lubricant and filling agent.The example of this adjuvant comprises: KBM-502, KBM-503, KBM-5103, KBM-802 and KBM-803 (by Shin-Etsu Chemical Co., Ltd. makes); BYK-333, BYK-307, BYK-3500, BYK-3530 and BYK-3570 (by BYK-Chemie Co., Ltd. makes), Z-6062, SH-6062 and SH-29PA (by Dow Corning Toray Co., Ltd. makes); And LA-82 (by Adeka Co., Ltd. makes).
[0019] can be under the temperature of room temperature to 80 ℃ in scope,, obtain ultraviolet ray of the present invention-curable resin combination by mixing and dissolving above-described independent component together and optionally filter the potpourri that so obtains afterwards.
The viscosity of the resin combination of ultraviolet ray of the present invention-curable adopts Brookfield viscometer to be measured as 30-800mPas and preferred 50-500mPas under 25 ℃.When viscosity during, may obtain the thickness evenness of 2P resin bed hardly and, may spend long centrifugal dishing out of time (spin off) resin, as a result deterioration throughput rate when viscosity during greater than 800mPas less than 30mPas.
Under DVD or HD-DVD CD situation, form transparent resin intermediate layer by following method (1): resin combination of the present invention is applied in transparent resin punch die and the substrate one of at least, wherein by the technology such as spin coating, screen printing or roller coat, the lamination first transparent resin substrate, first recording layer and first translucent reflective layer in described substrate, substrate bonded to one another afterwards and transparent resin punch die carry out the irradiation of ultraviolet then from transparent resin punch die side.Perhaps, can form transparent resin intermediate layer by following method (2): by above-described technology, with resin combination coating transparent resin punch die of the present invention, afterwards by the ultraviolet radiation, solidify this resin combination, the resin-bonded transparent resin punch die that adopts optional ultraviolet ray-curable then to substrate, wherein the lamination first transparent resin substrate, first recording layer and first translucent reflective layer in described substrate.Method for optimizing (2), this is because it allows the warpage of control multiplayer optical disk easily.The stripping performance angle is considered from the transparent resin punch die, also method for optimizing (2).In addition, in the blu-ray CD, form transparent resin intermediate layer in the mode identical with DVD or HD-DVD CD.Usually, polycarbonate resin is used for the first transparent resin substrate of 0.6mm in DVD or HD-DVD CD, perhaps is used for the resin base of 1.1mm in the blu-ray CD.Therefore, when using the transparent resin punch die of making by polycarbonate, consider method for optimizing (2) from the angle of stripping performance.
[0020] example that is used for the resin of transparent resin punch die comprises acryl resin, methacrylic resin, polycarbonate resin, polyolefin resin (especially, amorphous polyolefin), vibrin, polystyrene resin and epoxy resin.The performance of 2P resin after solidifying, for example angle of demolding performace, agent of low hygroscopicity energy and shape stability, especially preferably amorphous polyolefin; From the material cost angle, especially the transparent resin punch die that becomes of optimization polycarbonate resinon or amorphous polyolefin or polycarbonate resin can be used in the resin combination of ultraviolet ray of the present invention-curable.
Impinge actinic radiation ultraviolet ray of the present invention-curable resin combination will provide cured product.The example of actinic radiation comprises ultraviolet ray or near UV light.The example of actinic radiation sources comprises low pressure, high pressure or ultrahigh pressure mercury lamp, metal halide lamp, (pulse) xenon lamp, electrodeless lamp and ultraviolet emitting diode.Above-described cured product is also included within the present invention.
[0021] recording layer about forming on the transparent resin intermediate layer of being made by above-described cured product can use or organic dyestuff or phase-change material.The example of this organic dyestuff comprises metallic azo dyes, polymethin dyes and phthalocyanine dye.The example of this phase-change material comprises the material of being made by Sb and Te, and it contains one or more adjuvants that are selected among In, Ag, Au, Bi, Se, Al, P, Ge, H, Si, C, V, W, Ta, Zn, Ti, Ce, Tb, Sn and the Pb.
And resin combination of the present invention can be used for having and bonds the CD of this structure of polycarbonate substrate and blu-ray CD within it on the two.
Embodiment
[0022] hereinafter the DVD dish that forms of amorphous polyolefin resin by use being used for the transparent resin punch die or polycarbonate resin is described the present invention as an example.The invention is not restricted to the DVD dish, and may be used on HD-DVD and the blu-ray CD.
[0023]
Embodiment 1-12 and Comparative Examples 1
Preparation has shown in the table 1 the embodiment 1-12 that forms (weight portion) and the Comparative Examples 1 ultraviolet ray-curable resin combination in each.In addition, for embodiment 1-12 and Comparative Examples 1 each, preparation has the second ultraviolet ray-curable resin combination with first ultraviolet ray shown in the table 1-curable compositions same composition.
[0024]
Be noted that in the employed abbreviation of independent composition shown in the table as described below.
R-604: diox omega-diol diacrylate, by Nippon Kayaku Co., Ltd. makes.
R-684: tristane dihydroxymethyl diacrylate, by Nippon Kayaku Co., Ltd. makes.
TMPTA: trimethylolpropane triacrylate, by Ni ppon Kayaku Co., Ltd. makes.
T-1420 (T): the double trimethylolpropane tetraacrylate, by Nippon KayakuCo., Ltd. makes.
PET-30: pentaerythritol triacrylate, by Nippon Kayaku Co., Ltd. makes.
M-315: three [acryloxy ethyl] isocyanuric acid ester (by Toa Gosei Co., Ltd. makes).
DPHA: dipentaerythritol acrylate, by Nippon Kayaku Co., Ltd. makes.
TPGDA: tripropylene glycol diacrylate, by Cognis Co., Ltd. makes.
NPG-2P: neopentyl glycol gathers the propoxyl group diacrylate, and by Dai-ichi KogyoSeiyaku Co., Ltd. makes.
LA: lauryl acrylate, make by NFO Corp..
AM-30PG: methoxyl tripropylene glycol acrylate, by Shin-nakamura ChemicalCo., Ltd. makes.
FA-512A: dicyclopentenyl oxygen base ethyl propylene acid esters, by Hitachi ChemicalCo., Ltd. makes.
Irgacure 184:1-hydroxyl-cyclohexyl-phenyl ketone is made by Ciba SpecialtyChemicals K.K..
Speed TPO:2,4,6-trimethylbenzoyl diphenyl phosphine oxide.
[0025] (preparation of assess sample A and B)
Embodiment 1-12 and Comparative Examples 1 in each by following four kinds of method 1-4, by using gained ultraviolet ray-curable resin combination, preparation assess sample dish A.
(1) uses that to have track pitch be that 0.74 micron, table top (land) width are that 0.3 micron and table surface height are the diameter 120mm of uneven pattern form of 200 nanometers and the transparent resin punch die of thickness 0.6mm.This transparent resin punch die is become by alicyclic polyolefin (trade name ZEONOR1060R is made by Zeon Corp.) or polycarbonate resin.To the interior periphery supply 2.0g of transparent resin punch die ultraviolet ray-curable resin combination, and carry out spin coating, so that the thickness of 2P resin bed is 8 microns ± 2 microns.Afterwards, use high-pressure sodium lamp (80W/cm) at 600mJ/cm 2Ultraviolet ray-curable resin combination that following irradiation should be coated with is so that ultraviolet ray-curable resin combination solidifies.
(2) to the interior periphery supply 2.5g of the polycarbonate substrate (first substrate) of diameter 120mm and thickness 0.6mm KAYARAD DVD-575 (a kind of ultraviolet ray of in DVD, using-curable bonding agent, by Ni ppon Kayaku Co., Ltd. make), wherein in described polycarbonate substrate, form azo dye layers as first recording layer and first reflection horizon.Then, with the transparent resin punch die of preparation in above (1) be placed on supplied as on the curable bonding agent, its mode makes does not introduce bubble, and is bonded in first substrate in 4 seconds by carry out spin coating under 2000rpm.
(3) high-pressure sodium lamp (80W/cm) is at 400mJ/cm 2Under be used for from transparent resin punch die side irradiation, so solidify second ultraviolet ray-curable resin combination.
(4) with disk releasing means (by Origin Electric Co., Ltd. makes), make the demoulding of transparent resin punch die, preparation assess sample dish.
Notice that discovery is 50 microns ± 5 microns as the thickness of the transparent resin intermediate layer of the 2P resin bed and the second ultraviolet curing resin layer thickness sum.
Preparation assess sample dish B as described below: the operation of abideing by method (4) is identical with the operation of preparation assess sample dish A, and different is not to be formed on first recording layer and the reflection horizon that form among the assess sample dish A; Afterwards, be the preform of tetrafluoropropanol (TFP hereinafter referred to as) the solution coat assess sample dish B for preparing like this of the azo dyes of 600 nanometers with maximum absorption wavelength, forming thickness is the dye coating of 100 nanometers, so preparation assess sample dish B.
[0026], carries out following evaluation (I)-(IV) and, carry out following evaluation (V) by using the assess sample dish B that so obtains by using the assess sample dish A that so obtains.The result of acquisition like this has been shown in the table 2.Be noted that in principle, for each evaluation, repeat to estimate operation 2 times, with preparation table 2.
(I) performance of evaluation demoulding from the transparent resin punch die
Visual inspection transparent resin punch die and polycarbonate substrate the two and measure the occurrence rate of the fusible occurrence rate of transparent resin intermediate layer/not and occurrence rate that dye coating peels off/occurrence rate not.It is bonding that transparent resin intermediate layer does not take place, and the situation that dye coating peels off do not take place yet be labeled as 0 (well), and take place bondingly to be labeled as * (bad) with the situation of peeling off one or both of.
(II) estimate the performance that from the transparent resin punch die, shifts
Adopt scanning probe microscopy (SPI3800N/SPA300 is made by Seiko InstrumentsInc.), the transparent resin intermediate layer of the uneven design transfer of observing the transparent resin punch die on it.According to following formula derive uneven pattern transfer percentage (mesa width and table surface height) and shift percentage and be labeled as 0 (well) more than or equal to 95% situation, and transfer percentage is labeled as * (bad) less than 95% situation.
Shift the mesa width (0.3 micron) * 100 (%) of the mesa width ÷ transparent resin punch die of percentage (mesa width)=transparent resin intermediate layer
Shift the table surface height (200 nanometer) * 100 (%) of the table surface height ÷ transparent resin punch die of percentage (table surface height)=transparent resin intermediate layer
[0027] (III) estimates the warpage of disc substrate
Adopt Dr.Schenk Co., the Prometheus MT-146 that Ltd. makes, the warpage size of measuring samples dish.Under the 56mm radius, radial missing is less than or equal to 0.4 °, 0.4 °-0.8 ° and more than or equal to 0.8 ° situation be labeled as respectively ◎ (very good), 0 (good) and * (bad).
(IV) endurancing of the uneven pattern of Zhuan Yiing
Allow sample disc in the environment of 80 ℃ and 85%RH (relative humidity), to leave standstill 500 hours, adopt scanning probe microscopy afterwards, measure the shape of uneven pattern.According to following formula, derive each mesa width and table surface height before endurancing and percent change afterwards; This percentage is labeled as 0 (good) and this percentage less than 5% situation and is labeled as * (bad) more than or equal to 5% situation.
Change % (mesa width)=(mesa width before the mesa width-endurancing after the endurancing) ÷ endurancing mesa width * 100 (%) before
Change % (table surface height)=(table surface height before the table surface height-endurancing after the endurancing) ÷ endurancing table surface height * 100 (%) before
[0028] (V) anti-dye diffusion test
Carry out following test, in order that evaluation inhibition dye diffusion under high temperature and high humility arrives the ability in the transparent resin intermediate layer.
Allow sample disc B in the environment of 80 ℃ and 85%RH (relative humidity), to leave standstill 500 hours, wash dye coating fully with TFP afterwards.Disk after the visual inspection washing; Do not find that almost the situation that dyestuff absorbs is labeled as ◎ (very good), find that the situation of slight absorption is labeled as 0 (good) and finds that the situation of strong absorption is labeled as * (bad).
[0029] although the sample disc of being concerned about that is used to estimate corresponding to the part of one deck of multiplayer optical disk, can adopt the sample disc that is used to estimate to carry out the evaluation of transparent resin intermediate layer fully.
Can find out that according to the result shown in the table 2 resin combination of ultraviolet-curing of the present invention satisfies the desired performance of 2P resin aspect demolding performace from the transparent resin punch die and at transfer aspect of performance from the transparent resin punch die; Compare with the disk that obtains by the composition of the Comparative Examples 1 that does not contain (A) component, the gained disk is good aspect dish substrate warpage, good with the permanance of the uneven pattern that shifts, even under high temperature and high humility, have the dye diffusion ability that suppresses, and aspect demolding performace from the transparent resin punch die that becomes by polycarbonate resin and especially good aspect the warpage of dish substrate.
Figure A200780026193D00181
Figure A200780026193D00191
Figure A200780026193D00201
Figure A200780026193D00211
Industrial applicibility
[0034] cured product of the resin combination of ultraviolet-curable of the present invention such as Performance of the performance that from the transparent resin punch die, shifts and the demoulding from the transparent resin punch die and so on Therefore aspect of performance is good and can be used as in the multiplayer optical disk with at least two-layer recording layer Ming tree fat intermediate layer.

Claims (11)

1 is used for the ultraviolet ray-curable resin combination of multiplayer optical disk, and it comprises:
(A) diox glycol two (methyl) acrylate and/or tristane dihydroxymethyl two (methyl) acrylate and
(B) Photoepolymerizationinitiater initiater.
2. the ultraviolet ray that is used for multiplayer optical disk of claim 1-curable resin combination, it comprises that further (C) has the compound of at least two (methyl) acryloyl groups in its molecule.
3. the ultraviolet ray that is used for multiplayer optical disk of claim 2-curable resin combination, it comprises the weight with respect to whole resin combination, 15-85wt% (A) component, 0.1-10wt% (B) component, and 10-80wt% (C) component.
4. the ultraviolet ray that is used for multiplayer optical disk of claim 2-curable resin combination, it further comprises (D) single (methyl) acrylate compounds.
5. the ultraviolet ray that is used for multiplayer optical disk of claim 4-curable resin combination, it comprises the weight with respect to whole resin combination, 15-85wt% (A) component, 0.1-10wt% (B) component, 8-80wt% (C) component, and 5-40wt% (D) component.
6. any one the ultraviolet ray that is used for multiplayer optical disk-curable resin combination of claim 2-5, the compound (C) that wherein has two or more at least (methyl) acryloyl group in its molecule comprises one or more in the poly-propoxyl group diacrylate of trimethylolpropane triacrylate, pentaerythritol triacrylate, double trimethylolpropane tetraacrylate, three [acryloxy ethyl] isocyanuric acid ester, dipentaerythritol acrylate, tripropylene glycol diacrylate and neopentyl glycol.
7. any one the ultraviolet ray that is used for multiplayer optical disk-curable resin combination of claim 4-6, wherein (D) single (methyl) acrylate compounds comprises one or more in dicyclopentenyl oxygen base ethyl propylene acid esters, lauryl acrylate and the methoxyl tripropylene glycol acrylate.
8. any one the ultraviolet ray that is used for multiplayer optical disk-curable resin combination of claim 1-4, wherein Photoepolymerizationinitiater initiater (B) is 1-hydroxycyclohexylphenylketone or 2,4,6-trimethylbenzoyl diphenyl phosphine oxide.
9. any one the ultraviolet ray that is used for multiplayer optical disk-curable resin combination of claim 1-5, wherein adopting Brookfield viscometer is 30-800mPas in the viscosity of 25 ℃ of compositions of measuring down.
10. by with any one the cured product that the ultraviolet ray that is used for multiplayer optical disk-curable resin combination obtains of photochemical x ray irradiation x claim 1-6.
11. a multiplayer optical disk, it comprises the cured product of claim 10.
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